Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene

The reaction of mixtures of aryllithium regioisomers obtained either by directed lithiation or by Br/Li exchange with substoichiometric amounts of Cp(2)ZrCl(2) proceeds with high regioselectivity. The least sterically hindered regioisomeric aryllithium is selectively transmetalated to the correspond...

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Autores principales: Castelló‐Micó, Alicia, Herbert, Simon A., León, Thierry, Bein, Thomas, Knochel, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680335/
https://www.ncbi.nlm.nih.gov/pubmed/26586204
http://dx.doi.org/10.1002/anie.201508719
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author Castelló‐Micó, Alicia
Herbert, Simon A.
León, Thierry
Bein, Thomas
Knochel, Paul
author_facet Castelló‐Micó, Alicia
Herbert, Simon A.
León, Thierry
Bein, Thomas
Knochel, Paul
author_sort Castelló‐Micó, Alicia
collection PubMed
description The reaction of mixtures of aryllithium regioisomers obtained either by directed lithiation or by Br/Li exchange with substoichiometric amounts of Cp(2)ZrCl(2) proceeds with high regioselectivity. The least sterically hindered regioisomeric aryllithium is selectively transmetalated to the corresponding arylzirconium species leaving the more hindered aryllithium ready for various reactions with electrophiles. As an application, these regioselective transmetalations from Li to Zr were used to prepare all three lithiated regioisomers of 1,3‐bis(trifluoromethyl)benzene.
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spelling pubmed-66803352019-08-09 Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene Castelló‐Micó, Alicia Herbert, Simon A. León, Thierry Bein, Thomas Knochel, Paul Angew Chem Int Ed Engl Communications The reaction of mixtures of aryllithium regioisomers obtained either by directed lithiation or by Br/Li exchange with substoichiometric amounts of Cp(2)ZrCl(2) proceeds with high regioselectivity. The least sterically hindered regioisomeric aryllithium is selectively transmetalated to the corresponding arylzirconium species leaving the more hindered aryllithium ready for various reactions with electrophiles. As an application, these regioselective transmetalations from Li to Zr were used to prepare all three lithiated regioisomers of 1,3‐bis(trifluoromethyl)benzene. John Wiley and Sons Inc. 2015-11-20 2016-01-04 /pmc/articles/PMC6680335/ /pubmed/26586204 http://dx.doi.org/10.1002/anie.201508719 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Castelló‐Micó, Alicia
Herbert, Simon A.
León, Thierry
Bein, Thomas
Knochel, Paul
Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title_full Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title_fullStr Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title_full_unstemmed Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title_short Functionalizations of Mixtures of Regioisomeric Aryllithium Compounds by Selective Trapping with Dichlorozirconocene
title_sort functionalizations of mixtures of regioisomeric aryllithium compounds by selective trapping with dichlorozirconocene
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6680335/
https://www.ncbi.nlm.nih.gov/pubmed/26586204
http://dx.doi.org/10.1002/anie.201508719
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